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Sigma-Aldrich

Allylpalladium(II) chloride dimer

greener alternative

98%

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Synonym(s):
Bis((η3-allyl)(chloro)palladium), Di-ο-allyldi-μ-chlorodipalladium, [PdCl(C3H5)]2
Empirical Formula (Hill Notation):
C6H10Cl2Pd2
CAS Number:
12012-95-2
Molecular Weight:
365.89
Beilstein:
4124623
EC Number:
234-579-8
MDL number:
MFCD00044874
PubChem Substance ID:
24853328

Assay

98%

form

solid

reaction suitability

core: palladium
reaction type: Cross Couplings
reagent type: catalyst
reaction type: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

Aligned

storage temp.

2-8°C

SMILES string

Cl[Pd]CC=C.Cl[Pd]CC=C

InChI

1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2

InChI key

TWKVUTXHANJYGH-UHFFFAOYSA-L

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General description

Allylpalladium(II) chloride dimer is employed as catalyst in Heck reaction. It also participates as catalyst in the tandem nucleophilic allylation-alkoxyallylation reaction of the alkynylaldehydes with allyl chloride and allyltributylstannane.
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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Allylpalladium(II) chloride dimer has been employed for the following studies:
  • Synthesis of cationic palladium cataysts, used in the microwave-assisted Heck arylation.
  • Synthesis of N-heterocyclic carbene-palladium-η3-allyl chloride complexes, which are efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides.
  • Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.
  • As catalyst for greener Buchwald-Hartwig coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Radetich, B.; RajanBabu, T. V.
Journal of the American Chemical Society, 120, 8007-8007 (1998)
An N-heterocyclic carbene-palladium-η3-allyl chloride complex for the Suzuki-Miyaura coupling of aryl halides.
Broekemier NW, et al.
European Journal of Chemistry, 5(1), 162-166 (2014)
Superhydrophobicity of nanostructured carbon films in a wide range of pH values.
Lin Feng et al.
Angewandte Chemie (International ed. in English), 42(35), 4217-4220 (2003-09-23)
Yasuyuki Harada et al.
Organic letters, 7(20), 4385-4387 (2005-09-24)
[reaction: see text] The reaction of yne esters with carbon monoxide (1 atm) in the presence of palladium complexes gives bicyclic unsaturated lactone derivatives in good to high yields. The 2-pyridinyloxy group is a good leaving group among leaving groups
Suzuki cross-couplings of alkyl tosylates that possess beta hydrogen atoms: synthetic and mechanistic studies.
Matthew R Netherton et al.
Angewandte Chemie (International ed. in English), 41(20), 3910-3912 (2002-10-19)
View All Related Papers

Articles

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

Protocols

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M

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